most rewatched is cowboy bebop and Samurai Champloo. i’ve seen pretty much everything in my top 10 twice. Bebop i have seen a whopping 5 times. it is the greatest anime EVER and every time its on adult swim, i still watch it. Champloo i think i have seen 4 times, the music alone is reason enough to watch it over, and over and over.

i watched bebop for the first time junior year of high school, i think that was 2001, then i saw it again senior year on adult swin. the third time was freshman year of college was the first time i bought an anime on dvd, it was also the first time i watched all the episodes in order. it was at that moment that i realized there was something special about the anime medium. it was then i realized the difference between anime and “cartoons” between bebop and dbz. it was the moment i became an anime fan. 4th time i watched bebop was sophomore year… it was a really shitty year for me death in the family, failing organic chemistry, lady drama, and bebop was supremely comforting and it still is now. 5th time i saw it was senior year of college. I watched it to remind myself why i am losing my love for anime… i watched it to remind myself why nothing will ever top Bebop even after seeing atleast a 100 different shows since that fateful moment i first saw bebop. i have become so disenchanted with anime nowadays that i barely check for anything new.

>>i have become so disenchanted with anime nowadays that i barely check for anything new.

I think there’s still a lot to be discovered–how about more oldies/classics? But I agree it’s really difficult picking out the good ones from the ones that really waste your time, especially with the new shows.

My most re-watched series are:
1. Honey and Clover – love this series! But I do tend to re-watch the episodes with Nomiya in it more than the others. =D
2. Certain episodes of Detective Conan.
3. Minami-Ke (the first one) – I can randomly pick an episode anytime and still LOL at it.
4. Certain episodes of Darker than Black.

My most watched is Azumanga Daioh, my first bought anime series (aside from My Neighbor Totoro when I was 4…). I’ve seen it over ten times in the past three years and laugh at(/recite) every single joke and one liner. “Ding ding ding ding ding!” “…what was that…?” “A…bell?” “Like the kind you hear on game shows?” ^.^
Second most watched is probably sailor moon and Marimite, followed by Suzumiya (! if you’re getting bored with anime, try Suzumiya…o.0; it’s amazing. And out of order. Which is awesome.)
I also really like Utena and Sakura Taisen, but don’t get to watch them as often as I’d like. I’ve seen most of the Sailor Moon Episodes at least twice, Marimite twice and Utena once. ^^; I need a life.